Pompey will face Tottenham’s under-21 side at Fratton Park in the 2018/19 Checkatrade Trophy.
The Premier League club’s youngsters have been placed with the Blues in Southern Group A, which also contains Crawley and Gillingham.
Kenny Jackett’s men have two home games in the competition, with Spurs and Gillingham both visiting the south coast.
The first round of fixtures are scheduled to be played in the week beginning September 3, with matches following in the weeks beginning October 9 and November 12. However, there is a level of flexibility with these dates.
The 48 EFL clubs were placed into pre-determined groups, with consideration given to ensure travel time is minimised for supporters.
Southern Section
| Group A | Group B | Group C | Group D |
| Crawley | Cambridge | Newport | Bristol Rovers |
| Gillingham | Colchester | Plymouth | Exeter |
| Pompey | Southend | Swindon | Yeovil |
| Tottenham U21 | Southampton U21 | Chelsea U21 | West Ham U21 |
| Group E | Group F | Group G | Group H |
| Cheltenham | Northampton | AFC Wimbledon | Luton |
| Coventry | Oxford | Charlton | MK Dons |
| Forest Green | Wycombe | Stevenage | Peterborough |
| Arsenal U21 | Fulham U21 | Swansea U21 | Brighton U21 |
Northern Section
| Group A | Group B | Group C | Group D |
| Carlisle | Bury | Accrington | Crewe |
| Morecambe | Fleetwood | Blackpool | Shrewsbury |
| Sunderland | Rochdale | Macclesfield | Tranmere |
| Stoke U21 | Leicester U21 | West Brom U21 | Man City U21 |
| Group E | Group F | Group G | Group H |
| Burton | Barnsley | Doncaster | Lincoln |
| Port Vale | Bradford | Grimsby | Mansfield |
| Walsall | Oldham | Notts County | Scunthorpe |
| M'Brough U21 | Everton U21 | Newcastle U21 | Wolves U21 |